IL → FL · about 1,014 miles
Chicago to Winter Haven train schedule
Amtrak runs 7 direct trains a week from Chicago to Winter Haven. The fastest takes 41 hours 59 minutes; the first train leaves at 5:35 PM and the last at 6:40 PM.
Timetable data from · Schedule last changed
- Trains a week
- 7
- Fastest trip
- 41h 59m
- First train
- 5:35 PM
- Last train
- 6:40 PM
Timetable
Every train leaves from Chicago Union Station and arrives at Winter Haven. Times are local to each stop. Timetables published by tds.ai, refreshed October 15, 2026. Schedules change, so check times when you book.
| Departs | Arrives | Duration | Days | Rail company |
|---|---|---|---|---|
| 5:35 PM New | 1:39 PM +2 day | 43h 04m | Sun | Amtrak Full timetable |
| 6:40 PM | 1:39 PM +2 day | 41h 59m | Daily | Amtrak Full timetable |
Route map
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Where to board in Chicago Where you get off in Winter Haven The route of the busiest trip
Where to catch the train in Chicago
Where the train stops in Winter Haven
Return trip: Winter Haven to Chicago
Questions
How long is the train from Chicago to Winter Haven?
The fastest direct train takes 41 hours 59 minutes; the typical trip is 41 hours 59 minutes.
What time is the first train from Chicago to Winter Haven?
The earliest departure is at 5:35 PM (Sun) and the last at 6:40 PM (Daily).
Which rail companies go from Chicago to Winter Haven?
Amtrak runs direct trains on this route.
Where do I catch the train in Chicago?
Trains to Winter Haven leave from Chicago Union Station.